#------------------------------------------------------------------------------ #$Date: 2022-03-03 21:12:28 +0000 (Thu, 03 Mar 2022) $ #$Revision: 273261 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/93/4519354.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4519354 loop_ _publ_author_name 'Shafran, Yuri M.' 'Hussein, Aqeel A.' 'Beliaev, Nikolai A.' 'Shevyrin, Vadim A.' 'Shityakov, Sergey' 'Beryozkina, Tetyana V.' 'Bakulev, Vasiliy A.' _publ_section_title ; Selective Synthesis of Azoloyl NH-1,2,3-Triazoles and Azolyl Diazoketones: Experimental and Computational Insights. ; _journal_issue 6 _journal_name_full 'ACS omega' _journal_page_first 5008 _journal_page_last 5031 _journal_paper_doi 10.1021/acsomega.1c05898 _journal_volume 7 _journal_year 2022 _chemical_formula_moiety 'C10 H6 N6 O3' _chemical_formula_sum 'C10 H6 N6 O3' _chemical_formula_weight 258.21 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2021-06-22 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _cell_angle_alpha 91.354(10) _cell_angle_beta 92.008(9) _cell_angle_gamma 92.293(12) _cell_formula_units_Z 2 _cell_length_a 5.6104(7) _cell_length_b 5.7380(10) _cell_length_c 17.8464(17) _cell_measurement_reflns_used 753 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 23.3910 _cell_measurement_theta_min 3.8340 _cell_volume 573.53(13) _computing_cell_refinement 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-1997 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.5253 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -46.00 -21.00 1.00 100.00 -- 21.89 -64.00 -60.00 25 2 \w 55.00 89.00 1.00 100.00 -- 21.89 64.00 76.00 34 3 \w -46.00 5.00 1.00 100.00 -- -23.61 64.00 76.00 51 4 \w 18.00 44.00 1.00 100.00 -- -23.61 64.00 76.00 26 5 \w 32.00 98.00 1.00 100.00 -- 21.89-178.00 -30.00 66 6 \w -93.00 5.00 1.00 100.00 -- -23.61 -77.00-180.00 98 7 \w -100.00 -48.00 1.00 100.00 -- -23.61 178.00 30.00 52 8 \w -87.00 -3.00 1.00 100.00 -- -23.61 -64.00 -60.00 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0142702000 _diffrn_orient_matrix_UB_12 -0.0845938000 _diffrn_orient_matrix_UB_13 -0.0289498000 _diffrn_orient_matrix_UB_21 0.1192436000 _diffrn_orient_matrix_UB_22 0.0423224000 _diffrn_orient_matrix_UB_23 -0.0040846000 _diffrn_orient_matrix_UB_31 0.0400923000 _diffrn_orient_matrix_UB_32 -0.0797947000 _diffrn_orient_matrix_UB_33 0.0269777000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_unetI/netI 0.0796 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 5290 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 28.279 _diffrn_reflns_theta_min 3.428 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.41602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.495 _exptl_crystal_description plate _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.157 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 2804 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0550 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.1580 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1214 _reflns_number_total 2804 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_580 in P-1 exp_580.res created by SHELXL-2018/3 at 15:42:08 on 22-Jun-2021 CELL 0.71073 5.6104 5.738 17.8464 91.354 92.008 92.293 ZERR 2 0.0007 0.001 0.0017 0.01 0.009 0.012 LATT 1 SFAC C H N O UNIT 20 12 12 6 L.S. 10 PLAN 5 BOND $H HTAB fmap 2 acta 52 MORE -1 CONF OMIT 3 0 18 REM REM REM WGHT 0.040000 FVAR 0.83688 O1 4 1.078779 0.158508 0.117356 11.00000 0.08327 0.07194 = 0.08458 0.00381 0.00703 -0.01751 O2 4 1.211250 -0.120165 0.049023 11.00000 0.07705 0.12506 = 0.08335 -0.00113 0.03476 -0.00059 O3 4 0.855967 0.540357 0.399180 11.00000 0.05398 0.09234 = 0.08689 -0.02480 0.00407 0.00796 N1 3 0.951939 -0.030024 0.253383 11.00000 0.04119 0.06648 = 0.05512 -0.00436 0.00363 0.00199 N2 3 1.194438 -0.022679 0.262525 11.00000 0.04227 0.08873 = 0.06744 -0.01293 0.00067 0.00740 N3 3 1.250772 0.146110 0.310686 11.00000 0.04305 0.08817 = 0.05869 -0.01125 0.00141 0.00082 N4 3 1.079924 -0.044806 0.096075 11.00000 0.05619 0.08042 = 0.05572 0.00325 0.00620 -0.00228 N5 3 1.271636 0.730823 0.454458 11.00000 0.07114 0.08690 = 0.07362 -0.00899 -0.00317 -0.01440 N6 3 1.256430 0.891873 0.490803 11.00000 0.11239 0.09953 = 0.11607 -0.02674 -0.00323 -0.01800 C1 1 1.046272 0.453917 0.383476 11.00000 0.05047 0.07587 = 0.05310 -0.00246 0.00393 0.00001 C2 1 1.274965 0.542136 0.411389 11.00000 0.05495 0.08385 = 0.06195 -0.01547 -0.00096 -0.00469 C4 1 1.048123 0.245812 0.332921 11.00000 0.04064 0.07271 = 0.04922 -0.00015 0.00496 0.00194 C5 1 0.857731 0.132663 0.296735 11.00000 0.04037 0.06891 = 0.05404 -0.00616 0.00700 0.00449 C6 1 0.901358 -0.208853 0.126532 11.00000 0.04750 0.05573 = 0.05691 0.00085 0.00545 0.00165 C7 1 0.834087 -0.193320 0.200795 11.00000 0.04516 0.05818 = 0.05166 -0.00128 0.00364 0.00355 C8 1 0.654148 -0.341313 0.223638 11.00000 0.05478 0.07665 = 0.05759 0.00306 0.00853 -0.00530 AFIX 43 H8 2 0.607975 -0.333479 0.273147 11.00000 -1.20000 AFIX 0 C9 1 0.541204 -0.500895 0.174430 11.00000 0.06112 0.06855 = 0.08365 0.00554 -0.00049 -0.01333 AFIX 43 H9 2 0.416295 -0.596938 0.190255 11.00000 -1.20000 AFIX 0 C10 1 0.613057 -0.518206 0.101965 11.00000 0.07087 0.06312 = 0.07486 -0.00417 -0.00866 -0.00381 AFIX 43 H10 2 0.539048 -0.629206 0.069166 11.00000 -1.20000 AFIX 0 C3 1 0.793974 -0.372796 0.077124 11.00000 0.06602 0.07462 = 0.05716 -0.00680 0.00415 0.00107 AFIX 43 H3 2 0.842651 -0.385085 0.027957 11.00000 -1.20000 AFIX 0 H5 2 0.700120 0.147682 0.299381 11.00000 0.05813 H2 2 1.427244 0.484290 0.401613 11.00000 0.07007 HKLF 4 REM exp_580 in P-1 REM wR2 = 0.1580, GooF = S = 1.005, Restrained GooF = 1.005 for all data REM R1 = 0.0550 for 1214 Fo > 4sig(Fo) and 0.1446 for all 2804 data REM 180 parameters refined using 0 restraints END WGHT 0.0457 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y, z HTAB C5 N3_$1 EQIV $2 x+1, y, z HTAB C2 O3_$2 REM Highest difference peak 0.157, deepest hole -0.157, 1-sigma level 0.040 Q1 1 1.3020 -0.1989 0.1276 11.00000 0.05 0.16 Q2 1 1.4411 0.5784 0.4938 11.00000 0.05 0.15 Q3 1 0.9943 0.7337 0.4478 11.00000 0.05 0.15 Q4 1 1.0010 0.2312 0.2495 11.00000 0.05 0.14 Q5 1 1.1598 0.1966 0.2411 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0550 for 1214 Fo > 4sig(Fo) and 0.1446 for all 5292 data REM 180 parameters refined using n/a restraints REM Highest difference peak 0.16, deepest hole -0.16 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1446 REM R1_gt = 0.0550 REM wR_ref = 0.1580 REM GOOF = 1.005 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 5292 REM Reflections_gt = 1214 REM Parameters = 180 REM Hole = -0.16 REM Peak = 0.16 REM Flack = n/a ; _cod_data_source_file ao1c05898_si_002.cif _cod_data_source_block exp_580 _cod_database_code 4519354 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 98.01 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.22 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C8(H8), C9(H9), C10(H10), C3(H3) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.650 _oxdiff_exptl_absorpt_empirical_full_min 0.610 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0788(4) 0.1585(4) 0.11736(11) 0.0804(7) Uani 1 1 d . . . . . O2 O 1.2113(4) -0.1202(5) 0.04902(12) 0.0946(8) Uani 1 1 d . . . . . O3 O 0.8560(4) 0.5404(4) 0.39918(11) 0.0780(7) Uani 1 1 d . . . . . N1 N 0.9519(4) -0.0300(4) 0.25338(11) 0.0543(6) Uani 1 1 d . . . . . N2 N 1.1944(4) -0.0227(5) 0.26253(12) 0.0663(7) Uani 1 1 d . . . . . N3 N 1.2508(4) 0.1461(4) 0.31069(11) 0.0636(7) Uani 1 1 d . . . . . N4 N 1.0799(4) -0.0448(5) 0.09607(12) 0.0641(7) Uani 1 1 d . . . . . N5 N 1.2716(5) 0.7308(6) 0.45446(14) 0.0780(8) Uani 1 1 d . . . . . N6 N 1.2564(6) 0.8919(6) 0.49080(19) 0.1106(12) Uani 1 1 d . . . . . C1 C 1.0463(5) 0.4539(5) 0.38348(13) 0.0599(8) Uani 1 1 d . . . . . C2 C 1.2750(6) 0.5421(6) 0.41139(16) 0.0675(9) Uani 1 1 d . . . . . C4 C 1.0481(5) 0.2458(5) 0.33292(13) 0.0542(7) Uani 1 1 d . . . . . C5 C 0.8577(5) 0.1327(5) 0.29673(14) 0.0544(7) Uani 1 1 d . . . . . C6 C 0.9014(5) -0.2089(5) 0.12653(14) 0.0533(7) Uani 1 1 d . . . . . C7 C 0.8341(4) -0.1933(5) 0.20079(13) 0.0516(7) Uani 1 1 d . . . . . C8 C 0.6541(5) -0.3413(5) 0.22364(15) 0.0630(8) Uani 1 1 d . . . . . H8 H 0.607975 -0.333479 0.273147 0.076 Uiso 1 1 calc R U . . . C9 C 0.5412(5) -0.5009(6) 0.17443(17) 0.0716(9) Uani 1 1 d . . . . . H9 H 0.416295 -0.596938 0.190255 0.086 Uiso 1 1 calc R U . . . C10 C 0.6131(6) -0.5182(5) 0.10197(17) 0.0701(9) Uani 1 1 d . . . . . H10 H 0.539048 -0.629206 0.069166 0.084 Uiso 1 1 calc R U . . . C3 C 0.7940(5) -0.3728(6) 0.07712(15) 0.0661(8) Uani 1 1 d . . . . . H3 H 0.842651 -0.385085 0.027957 0.079 Uiso 1 1 calc R U . . . H5 H 0.700(5) 0.148(4) 0.2994(12) 0.058(8) Uiso 1 1 d . . . . . H2 H 1.427(5) 0.484(5) 0.4016(13) 0.070(9) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0833(17) 0.0719(17) 0.0846(15) 0.0038(13) 0.0070(11) -0.0175(13) O2 0.0770(17) 0.125(2) 0.0834(14) -0.0011(14) 0.0348(12) -0.0006(15) O3 0.0540(13) 0.0923(18) 0.0869(14) -0.0248(12) 0.0041(10) 0.0080(12) N1 0.0412(13) 0.0665(17) 0.0551(12) -0.0044(11) 0.0036(9) 0.0020(11) N2 0.0423(14) 0.089(2) 0.0674(14) -0.0129(14) 0.0007(10) 0.0074(13) N3 0.0431(14) 0.088(2) 0.0587(13) -0.0113(13) 0.0014(10) 0.0008(13) N4 0.0562(15) 0.080(2) 0.0557(14) 0.0033(13) 0.0062(11) -0.0023(15) N5 0.0711(18) 0.087(3) 0.0736(18) -0.0090(16) -0.0032(13) -0.0144(16) N6 0.112(3) 0.100(3) 0.116(2) -0.027(2) -0.0032(19) -0.018(2) C1 0.0505(18) 0.076(2) 0.0531(15) -0.0025(15) 0.0039(12) 0.0000(16) C2 0.055(2) 0.084(3) 0.0619(17) -0.0155(17) -0.0010(14) -0.0047(17) C4 0.0406(15) 0.073(2) 0.0492(14) -0.0001(13) 0.0050(11) 0.0019(14) C5 0.0404(16) 0.069(2) 0.0540(15) -0.0062(14) 0.0070(12) 0.0045(14) C6 0.0475(16) 0.0557(19) 0.0569(15) 0.0008(13) 0.0055(12) 0.0017(14) C7 0.0452(15) 0.0582(19) 0.0517(14) -0.0013(13) 0.0036(11) 0.0035(13) C8 0.0548(18) 0.077(2) 0.0576(16) 0.0031(15) 0.0085(13) -0.0053(16) C9 0.0611(19) 0.069(2) 0.084(2) 0.0055(17) -0.0005(16) -0.0133(16) C10 0.071(2) 0.063(2) 0.075(2) -0.0042(16) -0.0087(15) -0.0038(17) C3 0.066(2) 0.075(2) 0.0572(16) -0.0068(15) 0.0041(13) 0.0011(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_refln_index_h _diffrn_refln_index_k _diffrn_refln_index_l _diffrn_refln_intensity_net _diffrn_refln_intensity_u 0 0 -3 42.03 2.79 0 0 4 221.26 7.85 0 0 -4 233.04 7.88 0 0 -4 239.18 8.03 0 0 4 201.86 7.72 0 0 -4 210.9 7.96 0 0 4 226.83 7.79 0 0 5 620.42 16.88 0 0 -5 637.59 17.66 0 0 -5 680.76 17.01 0 0 5 643.33 16.85 0 0 -5 692.47 17.41 0 0 6 936.31 22.67 0 0 6 889.39 22.4 0 0 -6 911.12 23.66 0 0 7 9.44 2.13 0 0 7 10.19 2.19 0 0 -7 10.89 2.62 0 0 -8 5.36 1.88 0 0 8 3.91 1.33 0 0 8 4.19 1.68 0 0 9 -0.74 1.28 0 0 9 -1 0.88 0 0 -9 -0.17 1.29 0 0 10 185.97 10.67 0 0 10 194.25 11.1 0 0 -10 207.92 12.97 0 0 -11 24.6 4.59 0 0 11 20.88 3.76 0 0 11 19.18 3.59 0 0 -12 -0.37 1.52 0 0 12 0.3 0.73 0 0 12 0.59 0.58 0 0 -13 2.73 1.97 0 0 13 1 1.34 0 0 13 3.48 1.71 0 0 14 91.77 8.73 0 0 -14 107.43 10.81 0 0 14 82.62 8.49 0 0 15 8.91 2.97 0 0 15 4.6 2.09 0 0 -15 4.6 2.49 0 0 16 3.58 2.09 0 0 16 3.51 1.72 0 0 -16 2.02 1.7 0 0 -17 -1.11 2.07 0 0 17 0.69 1.2 0 0 17 0.65 0.69 0 0 -18 1.64 1.65 0 0 18 0.47 1.05 0 0 18 0.58 1.79 0 0 19 2.37 1.91 0 0 19 -0.33 1.06 0 0 20 1.58 1.52 0 0 20 1.85 1.65 0 0 -20 0.71 1.14 0 0 21 0.06 0.7 0 0 -21 1.12 1.45 0 0 -22 -1.83 1.97 0 0 22 -1.37 1.43 0 0 23 0 0.84 0 0 -23 -0.31 1.29 0 1 -23 0 1.74 0 -1 23 0.55 1.04 0 -1 22 -1.03 1.7 0 1 -22 1.07 0.87 0 1 -21 -0.18 1.27 0 -1 21 -1.74 1.65 0 1 -20 12.19 4.68 0 -1 20 4.46 2.39 0 -1 19 10.75 3.7 0 1 -19 16.52 4.87 0 1 -18 10.9 3.45 0 -1 18 6.69 2.74 0 1 -17 -1.94 1.86 0 -1 17 3.78 2.28 0 1 -16 3.35 2.56 0 -1 16 1.7 1.34 0 1 -15 8.22 3.22 0 -1 15 7.69 2.87 0 -1 14 -0.14 1.18 0 1 -14 2.17 1.36 0 -1 13 7.87 2.66 0 1 -13 8.39 3.13 0 -1 13 7.02 2.43 0 -1 12 5.47 2.23 0 -1 12 8.58 2.78 0 1 -12 3.79 2.13 0 1 -11 2.6 1.47 0 1 -11 2.77 0.82 0 1 -11 1.54 0.55 0 -1 11 3.91 2.12 0 -1 11 2.41 1.35 0 -1 10 11.88 2.71 0 1 -10 12.72 3.3 0 1 -10 12.71 1.53 0 1 -10 6.17 1.03 0 -1 10 9.77 2.42 0 1 -9 1.01 0.44 0 1 -9 0.64 0.42 0 1 -9 0.26 1.09 0 1 -9 0 0.35 0 -1 9 2.11 1.4 0 -1 9 4.47 2.24 0 1 -8 107.03 8.12 0 1 -8 105.21 4.73 0 -1 8 97.67 6.93 0 -1 8 109.66 7.97 0 1 -8 87.15 4.07 0 1 -7 30.42 2.48 0 -1 7 26.37 3.5 0 1 -7 31.45 3.85 0 1 -7 14.68 1.81 0 -1 7 30.18 4.09 0 1 -7 30.35 2.34 0 -1 6 120.19 8.01 0 1 -6 109.42 4.93 0 1 -6 102.21 4.65 0 1 -5 5330.07 91.47 0 1 -5 5599.84 92.4 0 -1 5 5513.69 96.89 0 -1 4 3926.94 72.26 0 1 -4 4022.46 68.8 0 1 -4 4116.04 69.52 0 1 -3 85.81 4.53 0 1 -3 92.44 4.99 0 -1 3 79.92 4.77 0 1 -3 100.1 5.37 0 1 -3 102.03 4.47 0 -1 2 1687.91 32.32 0 1 -2 1704.45 32.57 0 1 -2 1643.05 32.17 0 1 -2 1740.06 32.67 0 1 -1 103.54 4.12 0 1 -1 101.5 4.84 0 1 -1 106.95 4.7 0 1 0 85.14 3.09 0 1 1 514.24 12.49 0 1 1 474.46 12.52 0 -1 -1 489.65 12.34 0 1 1 487.98 12.65 0 1 2 5.83 0.99 0 1 2 8.48 1.24 0 1 2 9.34 1.18 0 -1 -2 2.41 0.66 0 1 3 353.55 11.14 0 1 3 363.25 10.53 0 1 3 386.34 8.62 0 1 3 355.02 10.09 0 -1 -4 101.8 5.23 0 1 4 144.73 5.43 0 1 4 143.6 5.64 0 1 4 129.79 4.8 0 -1 -5 182.92 8.56 0 1 5 189.16 6.67 0 1 5 184.53 6.61 0 1 5 181.4 6.37 0 -1 -6 429.64 15.1 0 -1 -6 410.86 12.75 0 1 6 425.27 12.3 0 1 6 412.96 10.85 0 1 6 426.96 10.8 0 1 6 451.19 13.49 0 1 6 415.2 10.62 0 1 7 -0.36 0.59 0 1 7 0.72 0.48 0 1 7 -0.1 0.25 0 1 7 -0.27 0.27 0 1 7 0.87 0.5 0 1 8 0.86 0.43 0 1 8 1.28 0.46 0 1 8 0.53 0.3 0 1 8 2.86 0.74 0 1 8 -0.39 0.81 0 -1 -8 0.34 0.9 0 1 9 87.05 3.72 0 1 9 124.17 7.78 0 -1 -9 108.55 8.43 0 1 9 119.26 7.18 0 1 9 86.55 3.58 0 1 10 155.12 4.85 0 1 10 183.9 9.66 0 1 10 195.42 10.46 0 -1 -10 181.57 11.47 0 1 10 142.88 4.64 0 1 11 0.34 0.22 0 -1 -11 -0.77 1.89 0 1 11 0.94 0.83 0 1 11 0.3 0.18 0 1 11 -0.57 0.72 0 -1 -12 4.12 2.02 0 1 12 3.11 1.46 0 1 12 6.18 2.19 0 1 13 136.83 10.23 0 -1 -13 120.87 11.1 0 1 13 108.69 8.72 0 1 14 10.79 2.99 0 -1 -14 12.82 3.81 0 1 14 10.86 2.72 0 1 15 0.49 1.03 0 1 15 -1.72 1.73 0 -1 -15 -0.56 1.72 0 1 16 46.83 6.29 0 -1 -16 63.04 9.06 0 1 16 56.82 7.12 0 -1 -17 4.57 2.47 0 1 17 5.42 2.19 0 1 17 3.37 1.63 0 -1 -18 3.32 2.1 0 1 18 3.66 1.98 0 1 18 3.16 1.85 0 1 19 -0.2 1.21 0 1 19 0.06 1.38 0 -1 -19 3 2.23 0 1 20 10.11 3.51 0 1 20 8.46 3.16 0 -1 -20 15.08 4.57 0 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1 88.12 4.92 0 2 -1 95.01 6.63 0 2 0 340.72 13.2 0 2 0 332.11 9.73 0 2 1 175.77 5.63 0 2 1 174.83 9.05 0 2 2 132.9 7.71 0 2 2 123.55 3.97 0 -2 -2 131.78 7.36 0 -2 -3 27.33 3.49 0 2 3 32.47 3.75 0 -2 -4 96.94 6.73 0 2 4 108.8 6.92 0 2 5 238.5 6.92 0 2 5 219.1 10.18 0 -2 -5 198.5 10.25 0 -2 -6 123.95 8.48 0 2 6 134.13 7.6 0 2 6 134.43 5.34 0 -2 -7 12.3 2.91 0 2 7 11.64 2.22 0 2 7 10.47 1.57 0 2 8 117.22 6.89 0 -2 -8 106.57 8.31 0 2 8 127.76 6.34 0 2 9 36.59 3.69 0 -2 -9 37.72 5.25 0 2 9 39.62 3.65 0 2 10 0.27 0.63 0 2 10 -1 0.73 0 -2 -10 0.17 0.9 0 2 10 -0.12 0.45 0 2 11 2.18 1.21 0 -2 -11 4.18 2.26 0 2 11 2.99 1.01 0 2 11 2.81 0.87 0 -2 -12 239.05 15.25 0 2 12 267.78 13.31 0 2 12 237.4 11.52 0 2 12 208.94 8.44 0 2 13 -0.32 0.87 0 2 13 -0.39 1.1 0 2 13 -0.75 0.59 0 -2 -13 0.87 1.68 0 2 14 105.77 8.3 0 2 14 117.31 9.52 0 -2 -14 120.51 11.55 0 2 15 21.97 4.24 0 2 15 17.86 3.45 0 -2 -15 21.58 5.25 0 2 16 -0.86 1.04 0 2 16 -0.15 1.14 0 -2 -16 -2.04 2.15 0 2 17 1.83 1.57 0 -2 -17 2.37 2.55 0 2 17 0.37 0.7 0 2 18 26.51 5.06 0 -2 -18 25.72 5.95 0 -2 -19 3.03 1.5 0 -2 -20 10.69 5.36 0 -2 -21 -1.58 3.45 0 -2 -22 4.82 3.36 0 3 -22 2.15 1.81 0 -3 22 0 0.45 0 3 -21 -2.02 1.7 0 -3 21 1.07 1.82 0 -3 20 0.28 0.79 0 3 -20 1.47 2.4 0 3 -19 -2.19 1.94 0 -3 19 2.39 2.23 0 3 -18 0.33 1.07 0 -3 18 2.31 2.24 0 -3 17 -1.25 1.9 0 3 -17 2.41 2.16 0 3 -16 0.63 0.99 0 -3 16 4.91 2.08 0 -3 15 2.14 0.91 0 3 -15 1.53 1.39 0 -3 14 17.55 4.56 0 3 -14 14 3.51 0 3 -14 21.12 3.56 0 -3 13 8.7 3.09 0 3 -13 6.83 1.97 0 -3 12 41.73 6.58 0 3 -12 35.96 4.62 0 -3 11 131.41 11.49 0 3 -11 126.02 9.07 0 -3 10 85.15 8.63 0 3 -10 80.34 7.24 0 3 -9 5.21 1.85 0 -3 9 5.8 2.15 0 3 -8 10.38 2.54 0 -3 8 8.17 2.5 0 -3 7 4.98 1.97 0 3 -7 2.42 1.27 0 3 -6 246.96 13.34 0 -3 6 249.43 13.48 0 -3 5 34.79 4.5 0 3 -5 35.1 4.77 0 -3 4 112.82 7.9 0 3 -4 116.49 9 0 3 -3 0.58 1.37 0 -3 3 0.37 0.62 0 3 -2 6.8 1.97 0 3 -1 1.83 1.6 0 3 0 366.62 16.37 0 3 0 362.54 11.65 0 3 1 18.1 2.04 0 3 1 16.18 2.83 0 3 2 28.32 4.21 0 3 2 30.66 2.37 0 3 3 28.05 4.19 0 -3 -3 28.82 4.2 0 3 3 26.77 1.95 0 3 4 638.86 22.17 0 -3 -4 610.43 21.71 0 3 4 590.17 12.01 0 3 5 42.42 5.09 0 -3 -5 43.71 5.64 0 3 6 4.33 1.38 0 -3 -6 2.37 1.01 0 3 6 4.9 0.67 0 3 7 101.54 7.96 0 3 7 98.9 3.9 0 -3 -7 91.39 8.21 0 -3 -8 20.3 3.87 0 3 8 21.02 3.61 0 3 8 19.39 1.82 0 3 9 2.97 0.82 0 3 9 3.57 1.52 0 -3 -9 3.96 2.45 0 3 10 168.56 10.33 0 3 10 163.2 7.1 0 -3 -10 158.65 12.19 0 3 11 -0.01 0.84 0 -3 -11 1.22 1.61 0 3 11 -0.02 0.3 0 3 12 21.61 3.41 0 -3 -12 19.92 4.75 0 3 12 20.02 3.81 0 3 12 18.42 2.67 0 3 13 79.79 7.66 0 -3 -13 75.69 9.09 0 3 13 67.14 5.95 0 3 14 1.6 1.06 0 -3 -14 3.38 1.19 0 3 15 15.21 3.65 0 -3 -15 9.97 3.2 0 -3 -16 -0.37 1.91 0 -3 -17 15.46 4.51 0 -3 -18 5.07 2.77 0 -3 -19 4.04 3.3 0 -3 -20 -5.77 3.29 0 -3 -21 -0.95 1.67 0 -4 20 2.76 2.12 0 4 -20 -3.6 2.2 0 -4 19 0 1.2 0 4 -19 -1.58 1.49 0 -4 18 3.13 2.84 0 4 -18 1.66 1.59 0 -4 17 0.98 1.61 0 4 -17 -0.61 1.24 0 4 -16 0.8 1.13 0 -4 16 -0.16 0.95 0 -4 15 9.32 3.54 0 4 -14 43.69 6.14 0 -4 14 38.68 6.8 0 -4 13 12.45 3.9 0 4 -13 14.51 3.26 0 4 -12 5.54 2.21 0 -4 12 6.71 2.61 0 -4 11 14.36 3.78 0 4 -11 17 3.81 0 4 -10 0.46 1.03 0 -4 10 0.71 1.04 0 4 -9 -1.1 1.29 0 -4 9 1.32 0.82 0 4 -8 38.24 6.03 0 -4 8 41.87 6.08 0 -4 7 33.2 5.22 0 4 -7 31.5 5.36 0 -4 6 4.61 1.95 0 4 -6 4.75 2.14 0 4 -5 0.1 1.29 0 4 -4 99.85 9.73 0 4 -3 2.55 0.79 0 4 -2 23.32 4.61 0 4 -1 84.67 8.97 0 4 0 8.87 3.26 0 4 1 0.74 1.1 0 4 2 1.23 0.61 0 4 2 -2 2.18 0 4 3 13.77 1.64 0 4 3 18.24 4.14 0 4 4 1.22 1.26 0 4 4 3.89 0.62 0 -4 -5 85.84 8.56 0 4 5 90.26 8.84 0 4 6 69.16 7.79 0 -4 -6 66.93 7.73 0 4 7 -1.44 1.37 0 -4 -7 -2.73 1.91 0 4 8 0.71 0.68 0 -4 -8 1.57 1.5 0 -4 -9 27.77 5.59 0 4 9 24.23 4.52 0 -4 -10 26.48 5.7 0 4 10 23.25 4.37 0 4 11 10.04 2.9 0 -4 -11 11.52 3.76 0 4 12 16.98 3.58 0 -4 -12 18.16 4.97 0 -4 -13 2.05 1.76 0 4 13 -0.3 1.4 0 -4 -14 -0.26 1.03 0 -4 -15 1.55 1.64 0 -4 -16 -0.2 1.05 0 -4 -17 3.55 3.45 0 -4 -18 1.14 1.51 0 -4 -19 3.9 2.86 0 5 -18 1.55 1.54 0 5 -17 -1.21 1.35 0 -5 15 6.02 3.25 0 5 -14 0.18 0.5 0 -5 14 0.55 1.72 0 5 -13 3.65 1.96 0 5 -12 6.76 2.6 0 5 -11 2.05 1.2 0 5 -10 -0.55 1.24 0 5 -9 3.05 1.85 0 5 -8 0.29 1.17 0 5 -7 1.19 1.2 0 5 -6 12.89 4.02 0 5 -5 2.45 1.84 0 5 -4 -0.9 1.05 0 5 -3 1.15 1.19 0 5 -2 5.78 2.68 0 5 -1 -2.24 1.95 0 5 0 0.14 0.97 0 5 1 34.57 6.23 0 5 2 18.16 4.68 0 5 3 2.94 1.89 0 5 4 0.1 1.17 0 5 5 4.2 1.97 0 5 6 53.12 7.62 0 5 7 5.34 2.19 0 -5 -8 17.53 4.43 0 5 8 16.85 4.17 0 -5 -9 0.55 0.84 0 5 9 0.81 0.66 0 -5 -10 -0.6 1.2 0 5 10 2.04 1.67 0 -5 -11 3.23 2.49 0 5 11 3.28 1.82 0 5 12 1.18 0.99 0 -5 -12 4.14 2.97 0 5 13 3.24 2.2 0 -5 -13 0.36 1.53 0 -5 -14 1.94 1.61 0 -5 -15 -1.11 2.64 0 -5 -16 1.51 3.06 0 -5 -17 -5.88 3.33 0 6 -13 0.98 1.26 0 6 -12 0 1.12 0 6 -11 0 0.75 0 6 -10 1.01 1.77 0 6 -9 -0.15 0.93 0 6 -8 2.46 2.18 0 6 -7 2.88 2.09 0 6 -6 1.46 2.41 0 6 -5 -1.56 1.88 0 6 -4 3.58 2.26 0 6 -3 1.75 1.66 0 6 -2 30.42 6.42 0 6 -1 2.37 1.3 0 6 0 6.85 2.86 0 6 1 47.23 7.79 0 6 2 -0.45 1.63 0 6 3 2.29 0.86 0 6 4 3.9 1.32 0 6 5 -1.72 1.07 0 6 6 6.61 2.67 0 6 7 0.81 2.03 0 6 8 -0.08 1.14 0 6 9 0.05 1 0 6 10 -0.36 1.14 0 6 11 0.04 0.59 0 6 12 1.19 1.62 0 -6 -12 4.83 2.93 0 -6 -13 1.57 1.92 0 -6 -14 1.15 1.81 0 7 -10 0 1.6 0 7 -9 0 1.73 0 7 -8 -4.8 2.95 0 7 -7 0 2 0 7 -6 0.66 1.28 0 7 -5 2.26 2.18 0 7 -4 0.03 1.23 0 7 -3 7.75 3.22 0 7 -2 0.32 0.95 0 7 -1 11.06 4.3 0 7 0 1.53 2.66 0 7 1 2.28 2.75 0 7 2 4.15 3.02 0 7 3 2.11 2.1 0 7 4 0.47 0.96 0 7 5 -4.48 2.69 0 7 6 1.11 1.42 0 7 7 0.97 1.36 0 7 8 0 1.11 -1 7 8 -3.57 2.53 -1 7 7 0.79 1.34 -1 7 6 -0.51 1.17 -1 7 5 1.71 1.8 -1 7 4 0.48 1.57 -1 7 3 2.79 2.32 -1 7 2 0.43 1.65 -1 7 1 3.2 2.8 -1 7 0 -0.46 1.66 -1 7 -1 11.15 4.51 -1 7 -2 7.34 4.24 -1 7 -3 0.61 1.97 -1 7 -4 -2.16 2.15 -1 7 -5 -0.01 1.7 -1 7 -6 0 1.39 -1 7 -7 3.28 2.62 -1 7 -8 0 1.69 -1 7 -9 0 1.39 1 -6 -14 0.25 1.57 1 -6 -13 0 1.66 -1 6 12 -0.53 1.36 1 -6 -12 1.5 1.66 -1 6 11 0.06 0.93 -1 6 10 -0.13 0.75 -1 6 9 0.67 1.55 -1 6 8 0.98 1.67 -1 6 7 0.56 1.3 -1 6 6 3.2 1.84 -1 6 5 2.5 1.95 -1 6 4 4.35 1.95 -1 6 3 7.08 3.25 -1 6 2 -1.04 1.14 -1 6 1 5.19 2.31 -1 6 0 1.87 1.91 -1 6 -1 1.79 2.26 -1 6 -2 1.72 1.9 -1 6 -3 0.18 0.81 -1 6 -4 -1.74 1.72 -1 6 -5 -1.04 1.07 -1 6 -6 -2.82 2.47 -1 6 -7 3.3 1.99 -1 6 -8 0.11 1.08 -1 6 -9 1.73 2.68 -1 6 -10 0.01 1.46 -1 6 -11 0 1.72 -1 6 -12 0 1.04 -1 6 -13 -1.06 1.38 1 -5 -17 1.43 1.76 1 -5 -16 1.54 1.94 1 -5 -15 -0.02 1.81 1 -5 -14 2.26 2.32 -1 5 13 -1.45 1.59 1 -5 -13 -0.22 1.48 1 -5 -12 0.49 1.07 -1 5 12 1.39 1.5 1 -5 -11 0.42 1.89 -1 5 11 2.03 1.94 -1 5 10 0.25 1.41 1 -5 -10 -0.37 1.43 -1 5 9 -0.55 1.45 1 -5 -9 1.76 1.49 -1 5 8 11.27 3.58 1 -5 -8 12.85 3.58 -1 5 7 23.88 5.11 -1 5 6 5.75 2.48 -1 5 5 6.58 2.62 -1 5 4 -2.47 2.14 -1 5 3 10.15 3.33 -1 5 2 2.87 1.95 -1 5 1 15.29 4.42 -1 5 0 2.32 1.6 -1 5 -1 2.13 2.06 -1 5 -2 15.25 4.29 -1 5 -3 -1.49 1.84 -1 5 -4 6.13 2.96 -1 5 -5 0.96 1.76 -1 5 -6 29.86 6.09 -1 5 -7 33.37 6.54 -1 5 -8 2.07 1.73 -1 5 -9 2.16 2.12 -1 5 -10 -0.55 1.72 -1 5 -11 0.28 1.37 -1 5 -12 1.43 1.11 -1 5 -13 5.73 2.66 -1 5 -14 7.08 2.91 -1 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21.78 5.23 5 1 -2 16.51 4.24 -5 -1 1 13.74 4.15 5 1 -1 18.07 4.78 -5 -1 0 -2.57 2.49 5 1 0 -1.25 1.55 -5 -1 -1 0.37 1.11 5 1 1 1.84 2.1 -5 -1 -2 7.64 3.18 5 1 2 5.38 1.76 -5 -1 -3 18.25 5.01 5 1 3 16.95 4.74 -5 -1 -4 17.4 4.76 5 1 4 20.12 4.97 5 1 5 150.85 14 -5 -1 -5 140.12 14.07 5 1 6 10.44 3.91 -5 -1 -6 10.2 3.88 5 1 7 39.17 6.93 -5 -1 -7 29.83 6.58 5 1 8 9.06 3.85 -5 -1 -8 2.17 1.51 -5 -1 -8 2.52 2.17 5 1 9 1.73 2.41 -5 -1 -9 3.89 2 -5 -1 -9 1.47 1.84 5 1 9 -0.47 0.82 5 1 10 7.51 2.8 -5 -1 -10 10.73 3.69 -5 -1 -10 5.84 2.91 5 1 10 9.66 3.76 5 1 11 1.29 1.72 -5 -1 -11 1.65 2.23 -5 -1 -11 0 0.79 5 1 11 2.53 2.19 5 1 12 1.89 1.63 5 1 12 -2.15 1.76 -5 -1 -12 2.08 1.73 5 1 13 -2.78 2.32 5 1 14 -2.7 2.29 5 1 15 1.08 2.1 5 1 16 -0.84 1.33 -5 -2 16 2.73 2.45 5 2 -16 2.7 2.17 -5 -2 15 14.78 5.49 5 2 -15 12.63 4.07 -5 -2 14 1.83 2.03 5 2 -14 1.84 1.42 5 2 -14 4.09 2.65 -5 -2 13 -0.02 1.1 5 2 -13 1.16 1.19 5 2 -13 0.46 1.74 -5 -2 12 4.94 3.52 5 2 -12 7.34 3.6 -5 -2 12 3.46 1.55 -5 -2 11 9.93 4.03 -5 -2 11 8.25 3.95 5 2 -11 11.34 3.91 -5 -2 10 18.54 5.69 5 2 -10 15.53 4.37 -5 -2 10 17.31 5.05 -5 -2 9 4.54 2.52 5 2 -9 0.73 1.47 -5 -2 9 3.54 2.65 -5 -2 8 16.24 5.19 5 2 -8 12.62 4.28 5 2 -7 29.12 6.55 -5 -2 6 0.84 1.8 -5 -2 5 5.94 2.84 -5 -2 4 -1.19 0.99 -5 -2 3 7.24 2.85 -5 -2 2 5.86 2.72 -5 -2 1 9.87 3.49 -5 -2 0 1.86 1.5 -5 -2 -1 42.21 7.24 -5 -2 -2 12.29 4.13 -5 -2 -3 69.3 9.62 -5 -2 -4 0.14 0.83 5 2 5 -0.37 1.45 -5 -2 -5 -0.1 0.84 5 2 6 -2.86 2.12 5 2 7 6.19 3.22 -5 -2 -8 2.4 1.96 5 2 8 6.92 3.04 -5 -2 -9 0.89 2.21 5 2 9 3.71 1.79 -5 -2 -9 1.2 0.88 -5 -2 -10 0 1.38 5 2 10 1.89 1.49 -5 -2 -10 1.34 1.47 5 2 11 -1.35 1.42 -5 -2 -11 2.3 1.94 -5 -2 -11 5.62 3.02 -5 -2 -12 -4.44 2.74 5 2 12 2.31 2 -5 -2 -12 2.64 2.16 5 2 12 0.73 1.54 -5 -2 -13 3.29 4.34 5 2 13 4.81 2.45 -5 -2 -14 0 1 5 2 14 1.84 2.59 5 2 15 1.88 1.94 -5 -2 -15 3.12 2.54 -5 -3 15 11.45 6.01 5 3 -15 5.99 3.03 -5 -3 14 2.13 2.1 5 3 -14 5.66 4.32 -5 -3 13 -0.6 1.26 5 3 -13 0.16 1.34 -5 -3 12 11.7 4.8 -5 -3 12 7.48 3.74 -5 -3 11 8.55 4.13 -5 -3 11 3.49 2.82 -5 -3 10 4.17 3.54 -5 -3 10 5.69 3.34 -5 -3 9 0.55 1.49 -5 -3 9 0.17 1.98 -5 -3 8 0.02 1.04 -5 -3 8 2.48 2.53 -5 -3 7 1.75 2.78 -5 -3 7 -0.18 1.12 5 3 -7 -0.44 1.29 -5 -3 6 2.43 3.05 -5 -3 6 4.05 2.95 5 3 -6 5.73 3.14 -5 -3 5 0.95 2.33 -5 -3 5 5.81 3.1 5 3 -5 1.01 1.24 -5 -3 4 33.09 7.23 -5 -3 4 18.85 5.84 5 3 -4 18.16 4.89 -5 -3 3 -3.39 2.86 5 3 -3 -3.47 2.05 -5 -3 2 5.85 3.18 5 3 -2 3.48 1.87 -5 -3 1 21.75 5.67 5 3 -1 14.82 4.25 -5 -3 0 1.73 2.51 5 3 0 1.55 1.58 -5 -3 -1 8.39 2.87 5 3 1 10.98 3.33 -5 -3 -2 2.6 1.46 5 3 2 1.97 1.56 -5 -3 -3 0.4 1.29 5 3 3 -3.94 2.39 -5 -3 -4 -2.55 2.25 5 3 4 -1.73 1.53 -5 -3 -5 -0.99 1.83 5 3 5 1.54 1.01 -5 -3 -6 0.22 1.73 -5 -3 -7 0.32 1.66 -5 -3 -8 5.44 3.17 -5 -3 -9 1.44 1.76 -5 -3 -10 0 0.69 5 3 11 2.34 2.14 -5 -3 -11 -4.29 2.93 5 3 12 1.27 1.53 -5 -3 -12 0 1.26 -5 -3 -13 19.7 6.24 -5 -4 12 3.13 2.55 -5 -4 12 2.55 2.33 5 4 -12 0 0.91 -5 -4 11 0 0.78 -5 -4 11 1.97 2.04 5 4 -11 0 0.76 -5 -4 10 0 0.68 -5 -4 10 0 0.86 5 4 -10 0 1.06 -5 -4 9 -0.77 1.32 -5 -4 9 -0.94 1.5 5 4 -9 -1.43 1.61 -5 -4 8 0 2.55 -5 -4 8 -2.08 2.17 -5 -4 7 0.37 0.76 5 4 -7 0.15 1.27 -5 -4 6 4.6 2.86 -5 -4 6 2.43 2.54 5 4 -6 -1.14 2.42 -5 -4 5 2.59 3.43 -5 -4 5 5.38 3.35 5 4 -5 6.99 3.02 -5 -4 4 -0.19 1.37 5 4 -4 1.95 2.15 -5 -4 3 12.16 4.51 5 4 -3 7.85 3.46 -5 -4 2 5 3.08 5 4 -2 4.92 3.09 -5 -4 1 3.32 1.87 5 4 -1 4.91 2.9 -5 -4 0 3.87 3.07 5 4 0 -1.71 2.35 -5 -4 -1 3.82 3.25 5 4 1 -2.36 2.34 -5 -4 -2 0.23 2.33 5 4 2 -0.63 0.83 -5 -4 -3 4.23 3.05 5 4 3 6.19 2.79 -5 -4 -4 -1.33 1.82 5 4 4 0.07 1.43 -5 -4 -5 4.01 2.89 5 4 5 4.57 2.42 -5 -4 -6 -2.42 2.24 5 4 6 1.8 1.9 -5 -4 -7 -4.4 3.02 5 4 7 0.34 1.01 -5 -4 -8 14.91 6.05 5 4 8 11.32 4.09 -5 -4 -9 0 1.38 5 4 9 2.62 2.48 -5 -4 -10 -3.03 2.63 -5 -4 -11 -1.33 1.8 5 5 -7 0 1.97 5 5 -6 0 1.2 5 5 -5 0 1.08 5 5 -4 0 2.4 5 5 -3 0.85 1.48 5 5 -2 3.43 2.93 5 5 -1 0.73 1.52 5 5 0 -4.03 2.68 5 5 1 4.06 3.64 5 5 2 0 1.13 5 5 3 5.69 3.63 5 5 4 3.39 2.44 5 5 5 -2.89 2.19 5 5 6 -6.01 3.08 6 -4 -8 0.22 0.76 6 -4 -7 1.47 2.41 6 -4 -6 2.4 2.11 6 -4 -5 1.9 2.5 6 -4 -4 5.74 3.12 6 -4 -3 1.33 2.06 6 -4 -2 2.92 2.41 6 -4 -1 -0.47 1.34 6 -4 0 -3.47 2.38 6 -4 1 0.05 0.7 6 -4 2 -2.11 1.91 6 -4 3 -7.4 3.4 6 -4 4 -0.87 1.26 6 -4 5 -4.95 2.8 6 -4 6 2.51 2.04 6 -4 7 0 0.61 6 -3 -11 1.59 1.69 6 -3 -10 1.5 1.64 6 -3 -9 -0.42 0.94 6 -3 -8 3.03 2.28 6 -3 -7 -0.02 1.2 6 -3 -6 5.22 3.26 6 -3 -5 3.68 2.78 6 -3 -4 -2.33 2.95 6 -3 -3 -2.17 2.04 6 -3 -2 1.66 1.73 6 -3 -1 2.32 1.57 6 -3 0 5.42 3.37 6 -3 1 4.27 2.65 6 -3 2 -3.02 2.49 6 -3 3 1.88 2.37 6 -3 4 0.49 1.05 6 -3 5 1.24 1.78 6 -3 6 0 0.79 6 -3 6 0.21 1.36 6 -3 7 -4.11 2.27 6 -3 7 4.08 2.53 6 -3 8 4.1 2.82 6 -3 8 2.58 2.04 6 -3 9 1.51 2.19 6 -3 9 0 1.96 6 -3 10 -0.9 1.2 6 -3 10 0 1.29 -6 2 13 -0.54 1.73 6 -2 -13 0 0.5 -6 2 12 1.29 1.91 6 -2 -12 3.3 3.12 -6 2 11 -2.01 1.99 6 -2 -11 1.18 2.12 -6 2 10 -0.51 1.15 6 -2 -10 0 1.77 6 -2 -9 -5.31 3 6 -2 -8 0.34 1.12 6 -2 -7 21.49 5.5 6 -2 -6 4.78 2.49 6 -2 -5 3.68 2.24 6 -2 -4 6.8 3.27 6 -2 -3 4.82 2.97 6 -2 -2 2.5 2.3 6 -2 -1 3.48 2.61 6 -2 0 -0.5 1.44 6 -2 1 0.95 1.75 6 -2 2 -1.92 1.36 6 -2 2 0.31 2.48 6 -2 3 1.91 1.55 6 -2 3 -0.98 1.82 6 -2 4 2.4 1.8 6 -2 4 -0.71 2.05 6 -2 5 0.93 1.39 6 -2 5 0.41 1.08 6 -2 6 1.23 1.84 6 -2 6 0.96 1.61 6 -2 7 2.27 2.21 6 -2 7 0.52 1.4 6 -2 8 1.47 1.49 6 -2 8 1.93 1.79 6 -2 9 0 1.91 6 -2 9 1.15 1.44 6 -2 10 0 0.85 -6 2 -10 0 2.22 6 -2 10 0 1.03 6 -2 11 2.72 2.13 -6 2 -11 0 2.2 6 -2 11 1.92 1.73 6 -2 12 0 1.12 -6 2 -12 -3.74 2.71 6 -2 12 -2.24 1.81 -6 1 13 0.07 0.64 6 -1 -13 -1.24 1.43 -6 1 12 -1.86 1.71 -6 1 11 1.71 1.71 -6 1 10 1.81 2.17 -6 1 9 4.85 3.21 -6 1 8 6.92 3.52 -6 1 7 4.41 2.88 -6 1 6 0.65 1.46 -6 1 5 2.87 2.33 -6 1 4 9.46 3.91 -6 1 3 -0.4 1.59 -6 1 2 -2.12 2.14 -6 1 1 0.67 2.59 6 -1 -1 -0.88 0.96 -6 1 0 -3.9 1.5 6 -1 0 2.75 1.99 6 -1 1 15.35 4.13 -6 1 -1 17.2 5.22 6 -1 2 5.37 2.68 -6 1 -2 8.49 3.95 6 -1 3 5.84 2.67 -6 1 -3 8.4 4.07 6 -1 4 -0.09 1.12 -6 1 -4 -1.09 2.38 6 -1 5 5.25 3.07 -6 1 -5 -0.39 1.33 6 -1 6 0.46 1.31 -6 1 -6 0.77 1 6 -1 7 0.2 2.01 -6 1 -7 0.25 2.37 6 -1 8 1.72 2.3 -6 1 -8 0 1.79 6 -1 9 -1.11 1.33 -6 1 -9 8.77 4.2 6 -1 10 0 1.18 -6 1 -10 4.62 3.04 6 -1 11 -0.85 1.22 -6 1 -11 1.32 1.71 6 -1 11 0.89 1.62 6 -1 12 0 0.98 -6 1 -12 0 1.62 6 -1 12 -3.46 2.27 6 -1 13 0 1.57 -6 0 14 -3.25 2.82 -6 0 13 -3.27 2.8 -6 0 13 0.39 1.22 -6 0 12 0.46 0.73 -6 0 11 0.15 1.4 -6 0 10 -1.62 1.79 -6 0 9 2.29 1.96 -6 0 8 2.33 1.96 6 0 -8 1.17 1.56 -6 0 7 0.39 0.94 6 0 -7 1.47 1.25 -6 0 6 -0.86 1.72 6 0 -6 -0.56 1.62 -6 0 5 5.35 3.04 6 0 -5 3.73 2.15 -6 0 4 28.87 6.4 6 0 -4 25.94 5.69 -6 0 3 0.19 1.42 6 0 -3 -1.26 1.71 -6 0 2 20.15 5.49 6 0 -2 22.18 5.5 -6 0 1 1.4 1.38 6 0 -1 5.02 2.25 -6 0 0 -0.21 1.25 6 0 0 3.54 2.4 -6 0 -1 9.72 4.02 6 0 1 11.95 4.25 -6 0 -2 3.04 2.53 6 0 2 4.99 2.81 -6 0 -3 2.23 2.04 6 0 3 -3.45 2.07 -6 0 -4 2.71 2.18 6 0 4 3.49 2.33 6 0 4 2.44 1.77 -6 0 -5 53.92 10.09 6 0 5 52.8 8.69 6 0 5 39.85 7.15 -6 0 -6 -3.46 2.69 6 0 6 2.1 1.5 6 0 6 -2.5 2.43 -6 0 -7 0.47 2.19 6 0 7 3.29 2.67 6 0 8 3.26 1.64 -6 0 -8 0.04 3.15 6 0 9 2.35 2.21 -6 0 -9 0 2.74 6 0 10 -2.07 1.92 -6 0 -10 0 0.7 -6 0 -11 0 2.16 6 0 11 -6.77 3.34 6 0 12 0 1.46 -6 0 -12 -2.93 2.28 6 0 13 -1.67 1.21 -6 -1 14 -3.28 2.79 -6 -1 13 10.24 5.67 6 1 -13 2.86 2.41 -6 -1 13 3.96 2.7 -6 -1 12 0.01 2.35 6 1 -12 1.94 2.81 -6 -1 12 -0.22 0.74 -6 -1 11 2.07 2.14 6 1 -11 -1.42 0.92 -6 -1 11 -3.42 2.4 6 1 -10 0.03 1.16 -6 -1 10 -2.21 2.39 6 1 -9 4.87 2.93 -6 -1 9 5.98 3.49 6 1 -8 0.97 1.79 -6 -1 8 1.34 1.49 6 1 -7 -0.86 2.23 -6 -1 7 2.43 2.02 6 1 -6 11.31 3.92 -6 -1 6 10.99 4.19 6 1 -5 15.74 5.27 -6 -1 5 21.6 5.84 6 1 -4 10.09 4.18 -6 -1 4 10.09 3.4 6 1 -3 0.58 1.14 -6 -1 3 0.75 1.48 6 1 -2 2.68 2.81 -6 -1 2 0.29 1.64 6 1 -1 -0.46 1.5 -6 -1 1 -1.17 2.08 6 1 0 18.06 5.48 -6 -1 0 11.96 4.22 6 1 1 7.42 2.95 -6 -1 -1 5.41 2.98 6 1 2 2.28 2.57 -6 -1 -2 5.47 3.18 6 1 3 8.62 3.25 -6 -1 -3 9.08 3.61 6 1 4 3.35 2.45 -6 -1 -4 3.77 2.92 6 1 5 -4.12 3.22 -6 -1 -5 -1.12 1.99 6 1 6 10.64 4.06 -6 -1 -6 7.18 4.32 6 1 7 1.35 1.46 -6 -1 -7 4.82 3 -6 -1 -8 0 1.25 6 1 8 0.46 1.51 6 1 9 0 1.4 -6 -1 -9 0 2.14 6 1 9 1.24 1.49 6 1 10 0.51 1.08 -6 -1 -10 0 1.85 6 1 10 -1.74 1.79 6 1 11 -2.63 2.18 6 1 11 0 1.2 6 1 12 -2.54 2.18 6 1 12 2.36 2.23 -6 -1 -12 6.4 3.29 -6 -2 13 2.96 2.63 -6 -2 13 -2.93 2.31 6 2 -13 -4.36 3 -6 -2 12 0 1.05 6 2 -12 -2.09 2.13 -6 -2 12 0 0.61 -6 -2 11 -2.26 2.29 6 2 -11 -0.33 0.99 -6 -2 11 2.13 2.31 -6 -2 10 6.17 4.14 6 2 -10 4.43 3.34 -6 -2 9 2.88 2.47 6 2 -9 -3.2 2.44 -6 -2 9 -3 2.29 6 2 -8 2.72 2.94 6 2 -7 -0.76 0.97 6 2 -6 2.09 2.7 -6 -2 6 0.07 1.17 6 2 -5 2.83 2.79 -6 -2 5 2.33 2.02 6 2 -4 10.48 4 -6 -2 4 4.27 2.52 6 2 -3 2.41 1.95 -6 -2 3 1.41 2.19 6 2 -2 1.88 1.75 -6 -2 2 4.94 3.17 6 2 -1 0.42 1.24 -6 -2 1 -0.96 1.1 6 2 0 3.6 2.42 -6 -2 0 4.17 2.93 6 2 1 7.75 3.56 -6 -2 -1 0.54 0.95 6 2 2 0 1.34 -6 -2 -2 2.71 2.23 6 2 3 3.09 1.82 -6 -2 -3 0.21 0.92 6 2 4 5.47 3.4 -6 -2 -4 1.79 2.44 6 2 5 1.94 1.55 6 2 6 0.98 1.07 6 2 7 0.34 0.97 6 2 8 0 0.62 -6 -2 -8 0 1.07 6 2 9 2.34 1.93 -6 -2 -9 0 1.28 -6 -2 -10 0 1.62 6 2 10 1.51 1.63 -6 -2 -11 0 1.6 6 2 11 0.41 0.95 6 2 11 1.17 2.21 -6 -3 10 -7.67 4.11 -6 -3 10 -4.76 3.12 6 3 -10 2.81 2.9 6 3 -9 -0.82 1.34 -6 -3 9 1.4 1.67 -6 -3 8 3.07 2.55 6 3 -8 0.57 1.23 -6 -3 8 5.19 4.21 -6 -3 7 0 1.26 6 3 -7 1.58 2.8 -6 -3 7 0 1.1 -6 -3 6 0 0.92 -6 -3 6 -5.2 3.22 -6 -3 5 3.05 3.17 -6 -3 5 0 1.89 -6 -3 4 -0.12 1.87 -6 -3 3 -4.53 3.69 -6 -3 2 -0.06 1.94 -6 -3 1 3.5 2.67 -6 -3 0 3.99 2.95 -6 -3 -1 2.91 2.59 -6 -3 -2 0.17 1.03 -6 -3 -3 -4.45 3.07 -6 -3 -4 1.47 2.8 6 3 4 2.94 2.64 6 3 5 4.19 2.93 -6 -3 -5 2.52 3.19 6 3 6 3.48 2.32 -6 -3 -6 0 1.97 6 3 7 0 1.08 -6 -3 -7 -4.27 3.12 6 3 8 2.53 2 -6 -3 -8 0 0.96 -6 -3 -9 5.04 3.35 6 3 9 5.91 3.78 -6 -4 6 2.66 2.2 -6 -4 5 9.73 5.02 -6 -4 4 -2.94 3.09 -6 -4 3 6.22 3.69 -6 -4 2 6.97 4.39 -6 -4 1 -1.67 2.19 -6 -4 0 4.22 3.47 -6 -4 -1 7.19 4.12 -6 -4 -2 2.73 2.54 -6 -4 -3 1.94 2.24 -6 -4 -4 -0.91 1.6 -7 2 7 0.85 1.65 7 -2 -7 4.95 3.1 -7 2 6 0.71 1.57 7 -2 -6 2.45 2.13 -7 2 5 7.02 4.85 7 -2 -5 5.74 3.24 -7 2 4 -2.49 2.96 7 -2 -4 2.73 2.67 -7 2 3 -2.19 2.4 7 -2 -3 1.26 2.79 7 -2 -2 4.87 3.71 -7 2 2 5.17 3.7 7 -2 -1 0.98 1.5 -7 2 1 1.03 2.07 7 -2 0 9.17 4.66 -7 2 0 0.55 1.38 7 -2 1 -2.74 2.28 -7 2 -1 1.51 1.97 7 -2 2 -1.46 1.68 -7 2 -2 0.91 1.8 -7 2 -3 -3.27 2.89 7 -2 3 0 1.52 -7 2 -4 2.49 2.48 7 -2 4 0 0.68 -7 2 -5 -5.77 3.75 7 -2 5 0 1.56 -7 1 8 0.12 2.45 -7 1 7 3.94 3.41 -7 1 6 5.1 4.02 -7 1 5 0 1.07 -7 1 4 5.98 4.47 -7 1 3 -2.19 2.32 -7 1 2 1.39 2.37 -7 1 1 3.51 3.19 -7 1 0 3.02 3.06 -7 1 -1 0.27 1.06 -7 1 -2 3.09 3.25 7 -1 3 0 0.92 -7 1 -3 4.2 3.21 7 -1 4 2.83 2.59 -7 1 -4 4.42 4.34 7 -1 5 0.46 1.6 -7 1 -5 -2.79 2.71 7 -1 6 8.3 4.58 -7 1 -6 0 3.15 7 -1 7 5.6 3.01 -7 1 -7 9.82 4.87 -7 0 9 -2.89 2.73 -7 0 8 0.74 1.83 -7 0 7 1.87 3.06 -7 0 6 -2.18 2.19 -7 0 5 0 0.65 -7 0 4 2.49 2.35 -7 0 3 0.27 1.05 -7 0 2 0 0.74 -7 0 1 9.34 4.85 -7 0 0 -0.79 1.52 -7 0 -1 1.63 2.38 7 0 1 0.25 1.33 -7 0 -2 2.35 2.94 7 0 2 -1.67 1.59 -7 0 -3 2.77 3.63 7 0 3 -4.35 2.57 -7 0 -4 0 1.62 7 0 4 0 0.98 -7 0 -5 6.92 5.93 7 0 5 2.46 3.22 7 0 6 -1.2 1.49 -7 0 -6 0 0.95 7 0 7 4.51 2.81 -7 0 -7 6.13 3.84 7 1 -8 2.09 2.06 -7 -1 8 2.58 2.66 7 1 -7 4.29 2.91 -7 -1 7 5.12 4.13 7 1 -6 -6.71 3.55 -7 -1 6 0.96 1.5 7 1 -5 5.86 3.32 -7 -1 5 -2.05 2.06 7 1 -4 -3.49 2.55 -7 -1 4 0 1.73 7 1 -3 3.33 3.25 -7 -1 3 -3.46 2.85 7 1 -2 1.56 1.9 -7 -1 2 3.08 2.54 7 1 -1 4.48 3.21 -7 -1 1 -2.83 2.62 7 1 0 10.9 4.57 -7 -1 0 8.67 4.67 7 1 1 0.94 1.78 -7 -1 -1 -2.97 2.59 7 1 2 5.28 2.33 -7 -1 -2 -2.01 2.23 7 1 3 7.91 3.77 -7 -1 -3 3.03 3.96 7 1 4 -5.75 3.22 -7 -1 -4 0 2.63 7 1 5 3.08 3.02 -7 -1 -5 2.46 3.24 7 1 6 0 1.52 7 1 6 0 0.83 7 2 -5 0 2.52 7 2 -4 5.29 4.23 7 2 -3 0 2.28 -7 -2 3 2.93 2.38 7 2 -2 2.02 1.96 -7 -2 2 2.7 2.86 7 2 -1 2.47 2.14 -7 -2 1 2.92 3.53 7 2 0 1.42 1.77 -7 -2 0 0 1.18 7 2 1 -3.31 2.49 -7 -2 -1 4.54 4.02 7 2 2 4.98 3.01 -7 -2 -2 4 3.41 7 2 3 -1.04 1.47 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C7 120.3(2) . . ? C5 N1 N2 110.6(2) . . ? C5 N1 C7 129.1(2) . . ? N3 N2 N1 106.7(2) . . ? N2 N3 C4 109.2(2) . . ? O1 N4 O2 124.7(3) . . ? O1 N4 C6 117.6(2) . . ? O2 N4 C6 117.6(3) . . ? N6 N5 C2 176.5(3) . . ? O3 C1 C2 124.0(3) . . ? O3 C1 C4 120.4(3) . . ? C2 C1 C4 115.6(3) . . ? N5 C2 C1 115.1(3) . . ? N5 C2 H2 116.6(16) . . ? C1 C2 H2 128.3(16) . . ? N3 C4 C1 123.8(2) . . ? N3 C4 C5 108.4(2) . . ? C5 C4 C1 127.6(2) . . ? N1 C5 C4 105.0(2) . . ? N1 C5 H5 122.5(16) . . ? C4 C5 H5 132.4(16) . . ? C7 C6 N4 122.0(2) . . ? C3 C6 N4 117.0(2) . . ? C3 C6 C7 121.0(3) . . ? C6 C7 N1 121.3(2) . . ? C8 C7 N1 120.1(2) . . ? C8 C7 C6 118.6(2) . . ? C7 C8 H8 119.5 . . ? C7 C8 C9 121.0(3) . . ? C9 C8 H8 119.5 . . ? C8 C9 H9 120.1 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C9 C10 H10 119.6 . . ? C9 C10 C3 120.7(3) . . ? C3 C10 H10 119.6 . . ? C6 C3 C10 118.8(3) . . ? C6 C3 H3 120.6 . . ? C10 C3 H3 120.6 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N4 1.219(3) . ? O2 N4 1.219(3) . ? O3 C1 1.233(3) . ? N1 N2 1.363(3) . ? N1 C5 1.335(3) . ? N1 C7 1.436(3) . ? N2 N3 1.301(3) . ? N3 C4 1.360(3) . ? N4 C6 1.474(3) . ? N5 N6 1.124(3) . ? N5 C2 1.314(4) . ? C1 C2 1.429(4) . ? C1 C4 1.480(4) . ? C2 H2 0.95(3) . ? C4 C5 1.362(3) . ? C5 H5 0.89(3) . ? C6 C7 1.392(3) . ? C6 C3 1.380(3) . ? C7 C8 1.372(4) . ? C8 H8 0.9300 . ? C8 C9 1.374(4) . ? C9 H9 0.9300 . ? C9 C10 1.371(4) . ? C10 H10 0.9300 . ? C10 C3 1.380(4) . ? C3 H3 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N4 C6 C7 -37.6(4) . . . . ? O1 N4 C6 C3 139.3(3) . . . . ? O2 N4 C6 C7 145.5(3) . . . . ? O2 N4 C6 C3 -37.6(4) . . . . ? O3 C1 C2 N5 -1.9(5) . . . . ? O3 C1 C4 N3 177.3(3) . . . . ? O3 C1 C4 C5 2.6(5) . . . . ? N1 N2 N3 C4 0.4(3) . . . . ? N1 C7 C8 C9 -179.2(3) . . . . ? N2 N1 C5 C4 0.8(3) . . . . ? N2 N1 C7 C6 -52.2(4) . . . . ? N2 N1 C7 C8 126.6(3) . . . . ? N2 N3 C4 C1 -175.6(2) . . . . ? N2 N3 C4 C5 0.1(3) . . . . ? N3 C4 C5 N1 -0.6(3) . . . . ? N4 C6 C7 N1 -6.0(4) . . . . ? N4 C6 C7 C8 175.3(3) . . . . ? N4 C6 C3 C10 -175.2(3) . . . . ? C1 C4 C5 N1 174.9(3) . . . . ? C2 C1 C4 N3 -2.7(4) . . . . ? C2 C1 C4 C5 -177.5(3) . . . . ? C4 C1 C2 N5 178.1(3) . . . . ? C5 N1 N2 N3 -0.8(3) . . . . ? C5 N1 C7 C6 125.6(3) . . . . ? C5 N1 C7 C8 -55.6(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 N1 N2 N3 177.4(2) . . . . ? C7 N1 C5 C4 -177.2(2) . . . . ? C7 C6 C3 C10 1.7(4) . . . . ? C7 C8 C9 C10 1.9(5) . . . . ? C8 C9 C10 C3 -1.7(5) . . . . ? C9 C10 C3 C6 -0.1(5) . . . . ? C3 C6 C7 N1 177.3(2) . . . . ? C3 C6 C7 C8 -1.5(4) . . . . ?